4-Nitrophenol → [2-Phenyl-1-thiophene-2-sulfonylaminoethyl]-phosphonic acid mono-(4-nitrophenyl) ester ammonium salt

HRID 1816218Notes

Reaction equation

[C:1]1([CH2:7][CH:8]([P:18](=[O:21])([OH:20])[OH:19])[NH:9][S:10]([C:13]2[S:14][CH:15]=[CH:16][CH:17]=2)(=[O:12])=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N+:22]([C:25]1[CH:30]=[CH:29][C:28](O)=[CH:27][CH:26]=1)([O-:24])=[O:23].ClC(Cl)(Cl)C#N>N1C=CC=CC=1>[NH4+:9].[N+:22]([C:25]1[CH:30]=[CH:29][C:28]([O:21][P:18]([CH:8]([NH:9][S:10]([C:13]2[S:14][CH:15]=[CH:16][CH:17]=2)(=[O:11])=[O:12])[CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)(=[O:19])[O-:20])=[CH:27][CH:26]=1)([O-:24])=[O:23]

Participants

Conditions

Temperature: 105 °C

Procedure

To sealed tube containing phosphonic acid (xiii) (50 mg; 0.14 mmol) and sublimed 4-nitrophenol (24 mg; 0.17 mmol) was added pyridine (0.7 mL) and trichloroacetonitrile (100 μL; 1.0 mmol). The reaction was heated to 105° C. for 6 hrs then was cooled and concentrated. The residue was purified by flash chromatography (chloroform-methanol-concentrated ammonium hydroxide; 8:2:0.25) to yield the ammonium salt 44 (36.4 mg, 52%) as a colorless solid: 1H NMR (400 MHz, CD3OD) δH 2.83 (td, J=9, 14 Hz, 1 H, CHPh), 3.23-3.29 (m, 1 H, CHPh), 3.95-4.02 (m, 1 H, NCHP), 6.85 (dd, J=4, 5 Hz, 1 H, Ar—H), 7.08-7.20 (m, 6 H, Ar—H), 7.27-7.31 (m, 2 H, Ar—H), 7.52 (dd, J=1.5, 5 Hz, 1 H, Ar—H), 8.12-8.16 (m, 2 H, Ar—H); 31P NMR: (162 MHz, CD3OD) δP 16.7; 13 C NMR: (100 MHz, CD3OD) δP 38.1, 122.0, 125.9, 127.3, 128.3, 129.2, 130.6, 132.2, 132.3, 144.4, 144.5.

Workup

customTo sealed tube
temperaturethen was cooled
concentrationconcentrated
customThe residue was purified by flash chromatography (chloroform-methanol-concentrated ammonium hydroxide; 8:2:0.25)

Sources & evidence

ORD record: ord-662f2890561147078b7ad480a05b75b8
Source dataset: uspto-grants-2005_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06884791B2

Reaction notes

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